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This paper discusses the incarceration of dissidents of Brazil’s military dictatorship (1964-1985) in penitentiaries, focusing on the gendered and resistance contours of this experience. It does so by analyzing the letters exchanged between two married political prisoners, Jessie Jane Vieira de Sousa and Colombo Vieira de Sousa Júnior. Jessie and Colombo were incarcerated for crimes against national security and spent nine years in three different penitentiaries to fulfill their sentences. Between 1964 and 1985, Brazil’s authoritarian government repurposed existing institutions and created new ones designed specifically for dissidence repression, like penitentiaries. Those charged with a national security crime were imprisoned in segregated quarters of the same facilities as prisoners whose crime fell under the Penal Code. I focus on letters exchanged by Jessie and Colombo between 1971 and 1973 to investigate their particular incarceration experiences as well as their shared experience of incarceration in a repressive legal system created by the military dictatorship. The correspondence between the two reveals how life was lived inside prison walls, after free political engagement was no longer an option. I argue that letter writing in political prisons is as much a personal endeavor as it is an act of resistance inside the system. First, I will explain how gender impacted their respective treatment and how it shaped the larger experience of prison life. Second, I will show how their particular experience within carceral institutions reveals other aspects of prison life. Finally, I will broaden the scope from a personal exchange to the imprisonment of male and female political prisoners in Rio de Janeiro state.